thioacetic acid S-(4-iodobenzyl) ester | 307537-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: thioacetic acid S-(4-iodobenzyl) ester
• 英文别名: 1-(S-acetylthiomethyl)-4-iodobenzene；4-(S-acetylthiomethyl)-1-iodobenzene；thioic acid S-(4-iodobenzyl) ester；1-acetylthiomethyl-4-iodobenzene；S-(4-iodobenzyl) thioacetate；S-(4-iodobenzyl)-thioacetate；1-Iodo-4-(S-acetylthiomethyl)benzene；S-[(4-iodophenyl)methyl] ethanethioate
• CAS: 307537-93-5
• 化学式: C₉H₉IOS
• 分子量: 292.14
• InChiKey: VFDFVTDPMDLFOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-(4-iodobenzyl) ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 5.0h， 生成 1-[(Benzyldisulfanyl)methyl]-4-iodobenzene
  参考文献：
  名称：

  Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake

  摘要：

  Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide functional group was responsible for the tumor growth inhibitory effects. Cu(I)-assisted radioiodination of benzyl 4-bromobenzyl disulfide gave benzyl 4-[I-123/I-125]iodobenzyl disulfide in 30-40% radiochemical yield. The radiolabeled disulfide was taken up by the cancer cells in a time-dependent manner, and the uptake was inhibited by the pretreatment of S-methyl methanethiosulfonate (MMTS), phorone and diallyl disulfide. This study suggested that the radiolabeled dibenzyl disulfide was taken up by the cancer cells via thiol-disulfide exchange and retained inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.002
• 作为产物：
  描述：

  4-碘苄醇 在 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 thioacetic acid S-(4-iodobenzyl) ester
  参考文献：
  名称：

  Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake

  摘要：

  Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide functional group was responsible for the tumor growth inhibitory effects. Cu(I)-assisted radioiodination of benzyl 4-bromobenzyl disulfide gave benzyl 4-[I-123/I-125]iodobenzyl disulfide in 30-40% radiochemical yield. The radiolabeled disulfide was taken up by the cancer cells in a time-dependent manner, and the uptake was inhibited by the pretreatment of S-methyl methanethiosulfonate (MMTS), phorone and diallyl disulfide. This study suggested that the radiolabeled dibenzyl disulfide was taken up by the cancer cells via thiol-disulfide exchange and retained inside the cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.002

文献信息

• Synthesis of “Porphyrin-Linker-Thiol” Molecules with Diverse Linkers for Studies of Molecular-Based Information Storage
  作者：Daniel T. Gryko、Christian Clausen、Kristian M. Roth、Narasaiah Dontha、David F. Bocian、Werner G. Kuhr、Jonathan S. Lindsey

  DOI：10.1021/jo000487u

  日期：2000.11.1

  efficient synthesis of 1-(S-acetylthio)-4-iodobenzene also has been developed. A set of porphyrins, each bearing one S-acetyl-derivatized linker at one meso position and mesityl moieties at the three remaining meso positions, has been synthesized. Altogether seven new aldehydes, eight free base porphyrins and eight zinc porphyrins have been prepared. The zinc porphyrins bearing the different linkers

  氧化还原活性分子（如卟啉）与电活性表面的连接为基于电可寻址分子的信息存储提供了一种有吸引力的方法。卟啉通过硫醇连接基很容易附着在金表面。电活性表面和卟啉之间的电子转移速率是决定适用于基于分子的存储器存储的关键因素之一。该速率取决于将硫醇单元连接至卟啉的接头的类型和长度。我们已经开发了具有八种不同连接子的硫醇衍生卟啉的制备方法。两组接头探讨了接头长度和缀合的影响，一组接头包含苯乙炔单元，而另一组接头包含烷基单元。一个缺电子的连接子具有四个直接与硫代苯基单元相连的氟原子。为了促进卟啉的合成，已经开发了便利的途径来制备具有受保护的S-乙酰硫基的多种醛。还开发了1-（S-乙酰硫基）-4-碘代苯的有效合成。合成了一组卟啉，每个卟啉在一个内消旋位置带有一个S-乙酰基衍生化的连接基，并在其余三个内消旋位置上带有均三甲苯基。总共制备了七个新的醛，八个游离碱卟啉和八个锌卟啉。带有不同接头的锌卟啉均通过原位裂
• A Convenient Synthesis of Thioacetates and Thiobenzoates Using Silica-Gel Supported Potassium Thioacetate
  作者：Tadashi Aoyama、Toshio Takido、Mitsuo Kodomari

  DOI：10.1081/scc-120025193

  日期：2003.11

  Abstract A simple and efficient procedure has been developed for the synthesis of thioesters by a reaction of alkyl halides with silica-gel supported potassium thioacetate or thiobenzoate under mild conditions.

  摘要 开发了一种简单有效的方法，通过烷基卤与硅胶负载的硫代乙酸钾或硫代苯甲酸钾在温和条件下反应合成硫酯。
• Ferrocenyl Oligo(phenylene‐vinylene) Thiols for the Construction of Self‐Assembled Monolayers
  作者：Christian Amatore、Stephen Gazard、Emmanuel Maisonhaute、Cécile Pebay、Bernd Schöllhorn、Jean‐Laurent Syssa‐Magalé、Jay Wadhawan

  DOI：10.1002/ejic.200700266

  日期：2007.9

  efficient preparation of conjugated oligo(phenylene-ethylene) thiols bearing redox-active ferrocene moieties is described. While minimising the number of synthetic steps, the proposed strategy permits the development of sets of oligomers with varying chain length. The redox properties of the compounds in solution are determined. Preliminary studies of self-assembled monolayers (SAMs) on gold electrodes are

  描述了带有氧化还原活性二茂铁部分的共轭低聚（亚苯基-亚乙基）硫醇的简短而有效的制备。在尽量减少合成步骤数量的同时，所提出的策略允许开发具有不同链长的低聚物组。测定溶液中化合物的氧化还原特性。讨论了金电极上自组装单层 (SAM) 的初步研究，表明通过 SAM 的电子转移确实很快。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of Well-Defined Tower-Shaped 1,3,5-Trisubstituted Adamantanes Incorporating a Macrocyclic Trilactam Ring System
  作者：Quan Li、Changshu Jin、Pavel A. Petukhov、Aleksey V. Rukavishnikov、Tatiana O. Zaikova、Avinash Phadke、Donald H. LaMunyon、Melissa D. Lee、John F. W. Keana

  DOI：10.1021/jo035640+

  日期：2004.2.1

  We describe the synthesis of two novel well-defined tower-shaped 1,3,5-trisubstituted adamantanes 30 and 33 that incorporate a macrocyclic trilactam ring system. Each nanoscale molecule has a broad tripodal base consisting of three identical sulfur-containing termini as the tripod feet, 4-acetylsulfanylmethylphenyl units in the case of 30 and 3,5-bis(acetylsulfanylmethyl)phenyl units in the case of

  我们描述了两个新的明确定义的塔形的1,3,5-三取代的金刚烷30和33的合成，其中结合了大环内酰胺环系统。每个纳米级分子都有一个由三个相同的含硫末端作为三脚架底脚组成的宽脚架基座，在30情况下为4-乙酰基硫烷基甲基苯基单元，在33情况下为3,5-双（乙酰基硫烷基甲基）苯基单元。硫原子被设计为通过形成三个S-Au键将分子三价键合至镀金商品AFM尖端的顶点。刚性金刚烷衍生的头部单元在顶部具有单个氢原子，旨在扫描样品。分子30和33通过一系列涉及末端炔烃和碘代芳基的Sonogashira偶联反应，由1,3,5-三乙炔基金刚烷酰胺合成。大环三内酰胺单元被包括在内以增加刚度。我们证明了分子30足够大且坚固，可以通过常规AFM尖端进行可视化。这些纳米级分子也可以作为化学上明确定义的纳米级对象用于AFM尖端的校准。
• Preparation, Characterization, and Electrical Properties of a Self-Assembled meso-Pyridyl Porphyrin Monolayer on Gold Surfaces
  作者：Amarchand Sathyapalan、Anup Lohani、Sangita Santra、Saurabh Goyal、M. Ravikanth、Soumyo Mukherji、V. Ramgopal Rao

  DOI：10.1071/ch05176

  日期：——

  A meso-pyridyl porphyrin, 5-(4-(2-(4-(S-acetylthiomethyl)phenyl)ethynyl)phenyl)-10,15,20-tris(4-pyridyl) porphyrin was synthesized by coupling of 5-4-ethynyl}phenyl-10,15,20-tris(4-pyridyl) porphyrin with 4-(S-acetylthiomethyl)-4-iodobenzene under mild palladium coupling conditions. The meso-pyridyl porphyrin was used for the preparation of self assembled monolayers on gold substrates. The gold substrates

  由5-在温和的钯偶联条件下，4-乙炔基}苯基-10,15,20-三(4-吡啶基)卟啉与4-(S-乙酰硫甲基)-4-碘苯。内消旋吡啶基卟啉用于在金基底上制备自组装单分子层。金基板是通过在氧化的 Si(100) 表面上热蒸发金制成的。使用基态紫外吸收和 X 射线光电子能谱 (XPS) 技术以及扫描探针显微镜 (SPM) 技术对自组装单分子层 (SAM) 进行了表征。与在 CHCl3 溶液中的卟啉相比，卟啉单层的紫外吸收光谱在 Soret 带中显示出 10 nm 的红移。这表明卟啉分子在金基板上并排排列。XPS 结合能的典型变化表明，卟啉的硫醇盐物质化学吸附到表面是通过强硫-金键合机制发生的。通过分子分辨率原子力显微镜 (AFM) 观察到碱性六方 (√3×√3) R 30° 有序自组装内消旋卟啉单分子层。通过扫描隧道光谱 (STS) 在不同的设定点电流下收集室温电流 - 电压 (I-V) 光谱